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- W1569289710 abstract "Reaction of α-enones 1a-g with acetonitrile anion 5, in THF at −80° gives, irreversibly, alcohols 7 or 11, resulting from carbonyl carbon attack, whatever the associated cation is (K+ or Li+). The reaction is considered to be under charge control. In THF, lithiated phenylacetonitrile 6 gives the alcohols 8 and 12 under kinetic control with benzalacetone 1b, 2-cyclohexenone 1d and 3-methyl 2-cyclohexenone 1e. Lithium alcoholate formation is reversible and ketones 10b, 14a and 14b formation, resulting from carbon 4 attack, is thermodynamically controlled. The other α-enones studied lead, under the same reaction conditions, to ketones 10a, 10c, 14c and 14d only. In a THF-HMPA mixture, reagent 6 only gives the starting α-enone, ketones 10 and 14. The lower lying the α-enone LUMO level, the faster the reaction, which indicates, in the present case, that the transition state for carbon carbon double bond attack occurs relatively early in the reaction path." @default.
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- W1569289710 date "1978-01-01" @default.
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- W1569289710 title "Factors controlling the regioselectivity of additions to α-enones—VI" @default.
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